p-Toluenesulfonic acid → HCID 12110021, compound

HRID 1057888Notes

Reaction equation

HRID 1057888 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[Cl:12][C:13]1[CH:14]=[N:15][CH:16]=[C:17]([Cl:35])[C:18]=1[CH2:19][CH:20]([C:22]1[C:27]2[CH2:28][C:29]([CH3:32])([CH3:31])[O:30][C:26]=2[C:25]([O:33][CH3:34])=[CH:24][CH:23]=1)O.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[Cl:12][C:13]1[CH:14]=[N:15][CH:16]=[C:17]([Cl:35])[C:18]=1/[CH:19]=[CH:20]/[C:22]1[C:27]2[CH2:28][C:29]([CH3:32])([CH3:31])[O:30][C:26]=2[C:25]([O:33][CH3:34])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 22734123HCID 22734123, compound

Product 1

HCID 12110021HCID 12110021, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

p-Toluenesulfonic acid (0.8 g) was added to a suspension of Compound 45a (1.0 g) obtained in Step A of Example 45 in toluene (27 ml), followed by heating under reflux for 30 minutes. After being allowed to stand for cooling, a saturated aqueous solution of sodium bicarbonate was added to the reaction solution for neutralization, followed by extraction with ether. The organic layer was washed with a saturated saline and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography (chloroform/methanol=20/1) to give Compound 67 (0.59 g, 62.2%) as yellow crystals.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 30 minutes
  3. temperaturefor cooling
  4. extractionfollowed by extraction with ether
  5. washThe organic layer was washed with a saturated saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe resultant residue was purified by silica gel column chromatography (chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-35aa6d8adfb64778bdce33d6bcd74158
Source dataset
uspto-grants-2003_02
Patent number
US06514996B2

Reaction notes

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